34671-09-5Relevant academic research and scientific papers
Dimethyl 3,4,5,5-tetraphenyl-1,3-thiazolidine-2,2-dicarboxylate and 3,3-dichloro-2,2,4,4,3′-pentamethyl-r-2′,t-4′- diphenylcyclobutane-1-spiro-5′-1,3-thiazolidine
Domagala, Malgorzata,Palusiak, Marcin,Pfitzner, Arno,Zabel, Manfred,Urbaniak, Katarzyna,Mloston, Grzegorz,Grabowski, Slawomir J.
, p. o595-o599 (2007/10/03)
The first of the title compounds, C31H27NO 4S, (V), crystallizes in the monoclinic space group P21c with two independent molecules in the asymmetric unit, while the second, C 23H27Cl2NS, (IX), crystallizes in the orthorhombic space group Pbca with one molecule in the asymmetric unit. In both crystal structures, the 1,3-thiazolidine ring adopts a half-chair conformation. The crystal structures are stabilized by weak C-H· · ·O and C-H· · ·Cl hydrogen bonds in (V) and (IX), respectively.
1,3-Thiazolidine-dicarboxylates from thioketones and thermally generated azomethine ylides
Mloston, Grzegorz,Urbaniak, Katarzyna,Heimgartner, Heinz
, p. 2056 - 2064 (2007/10/03)
The reaction of 9H-fluorene-9-thione (1) with the cis- and trans-isomers of dimethyl 1-(4-methoxyphenyl)- Saziridine-2,3-dicarboxylate (cis- and trans-2, resp.) in xylene at 110° yielded exclusively the spirocyclic cycloadduct with trans- and cis-configurations, respectively (trans- and cis-3; resp.; Scheme 1). Analogously, less-reactive thioketones, e.g., thiobenzophenone (5), and cis-2 reacted stereoselectively to give the corresponding trans-1,3-thiazolidine-2,4-dicarboxylate (e.g., trans-8; Scheme 2). On the other hand, the reaction of 5 and trans-2 proceeded in a nonstereoselective course to provide a mixture of trans- and cis-substituted cycloadducts. This result can be explained by an isomerization of the intermediate azomethine ylide. Dimethyl 1,3-thiazolidine-2,2-dicarboxylates 14 and 15 were formed in the thermal reaction of dimethyl aziridine-2,2-dicarboxylate 11 with aromatic thioketones (Scheme 3). On treatment of 14 and 15 with Raney-Ni in refluxing EtOH, a desulfurization and ring-contraction led to the formation of azetidine-2,2-dicarboxylates 17 and 18, respectively (Scheme 4).
Reaction d'aziridines, ylures d'azomethine potentiels, avec des cetophosphorannes. Obtention de pyrrolines-3
Vaultier, Michel,Danion-Bougot, Renee,Tonnard, Francois,Carrie, Robert
, p. 803 - 808 (2007/10/02)
The reaction of β-cetophosphoranes with azomethine ylides obtained by ring opening of 2,2-dimethoxycarbonyl aziridines is studied.Two competitive pathways are observed with the acetylmethylene phosphorane: a nucleophilic addition and a cycloaddition on the pseudo double bond of the phosphorane.In the case of the benzoylmethylene phosphorane, we observe only the cycloaddition reaction.The mechanisms of these reactions are discussed.The reaction of cycloaddition raises a theoretical problem which is still unsolved.
ADDITION D'YLURES D'AZOMETHINE AUX METHOXYCARBONYL CYCLOPENTENES ET CYCLOHEXENES BENZOCONDENSES. DIASTEREOSELECTIVITE DE LA CYCLOADDITION
Verbel, Joel,Gree, Danielle,Carrie, Robert
, p. 939 - 944 (2007/10/02)
Azomethine ylids add stereospecifically to 3-methoxycarbonyl-1-2-dihydronaphtalenes substituted in the 1 or 2 position.The diastereospecificity of the reaction is discussed.The behaviour of 2- or 3- methoxycarbonyl indenes and of 4-methoxycarbonyl-1,2-dihydronaphtalene is also studied.
Some Approaches to the Synthesis of Kainic Acid
Husinec, Suren,Porter, Alexander E. A.,Roberts, James S.,Strachan, Calum H.
, p. 2517 - 2522 (2007/10/02)
A strategy for the synthesis of the anthelmintic kainic acid is described, involving an investigation of the cycloaddition reactions of some azomethine ylides obtained from the thermal ring opening of aziridines and 4,5-dihydro-1,2,3-triazoles, with
